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Ring Expansion of Oxyglycals. Synthesis and Conformational Analysis of Septanoside-Containing Trisaccharides

Ganesh, N Vijaya and Raghothama, S and Sonti, R and Jayaraman, N (2010) Ring Expansion of Oxyglycals. Synthesis and Conformational Analysis of Septanoside-Containing Trisaccharides. In: Journal of organic chemistry, 75 (1). pp. 215-218.

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Official URL: http://pubs.acs.org/doi/abs/10.1021/jo901945e

Abstract

Oxyglycals, derived from lactose and maltose, were expanded to trisaccharides through a ring expansion method. Trisaccharides with 6-7-5 and 6-7-6 ring sizes were prepared through the ring expansion method, with high diastereoselectivities, in each step of their synthesis. The NOE and ROESY NMR spectroscopies were used to assess the dipolar Couplings within the trisaccharide. A computational study was undertaken, from which low energy conformations, as well as, dihedral angles that define the glycosidic linkages were identified.

Item Type: Journal Article
Additional Information: Copyright for this article belongs to American Chemical Society.
Department/Centre: Division of Chemical Sciences > Organic Chemistry
Division of Chemical Sciences > NMR Research Centre (Formerly SIF)
Date Deposited: 12 Jan 2010 08:58
Last Modified: 19 Sep 2010 05:54
URI: http://eprints.iisc.ernet.in/id/eprint/25367

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